Primary amine/CSA ion pair: A powerful catalytic system for the asymmetric enamine catalysis

Chen Liu, Qiang Zhu, Kuo-Wei Huang, Yixin Lu

Research output: Contribution to journalArticlepeer-review

69 Scopus citations

Abstract

A novel ion pair catalyst containing a chiral counteranion can be readily derived by simply mixing cinchona alkaloid-derived diamine with chiral camphorsulfonic acid (CSA). A mixture of 9-amino(9-deoxy)epi-quinine 8 and (-)-CSA was found to be the best catalyst with matching chirality, enabling the direct amination of α-branched aldehydes to proceed in quantitative yields and with nearly perfect enantioselectivities. A 0.5 mol % catalyst loading was sufficient to catalyze the reaction, and a gram scale enantioselective synthesis of biologically important α-methyl phenylglycine has been successfully demonstrated. © 2011 American Chemical Society.
Original languageEnglish (US)
Pages (from-to)2638-2641
Number of pages4
JournalOrganic Letters
Volume13
Issue number10
DOIs
StatePublished - May 20 2011

ASJC Scopus subject areas

  • Biochemistry
  • Organic Chemistry
  • Physical and Theoretical Chemistry

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